Hi Michael,
I agree with all of your assessments.
I singled out #5 as it's the least interesting on a course full of interest. I agree that its place at #5 balances a front nine full of difficult holes like 1, 3, 4, and 8. 2, 5, 6, and 7 balance the 9 with easier holes, but each has an aspect to grab those looking for an easy birdie. #2 has its wicked green, #5 has long grass right off the tee, and the stream left of the green. #6 has the strategic stream placement, and a steep fall-off to the left of the green. #7 is a true postage stamp, with the meandering stream only 2-3 paces from the front right edge.
Another unique aspect is that the front 9 is the more difficult part of the course, with the back nine shorter and a par 34. Many New England layouts follow the pattern of short, easy, open front nine with a longer, narrower, wooded back nine. Essex turns it around, letting you make up shots on the way in.
As for #14, the best-reproduced character aspect from the old green to the new is the sense that putts from the front half and back half are both downhill towards the "swale." From the back, this is true, but from the front, the optics hide the fact that putting is level or even slightly uphill.
Michael P, I'd have to go with #8 as the most difficult hole at Essex. A crazy fairway with the best angle to the green closest to OB, the slopes between fairway tiers cut as rough can cause a baseball swing or two from the middle of the fairway...and a wild green where shots hitting in the middle can bound into a pot bunker! My least favorite shot is the annoying tee shot at #13, but the wildly creative green makes up for it.